Great fortunes were made and suddenly lost here in the crash of 1929, the end of Winnipeg’s financial heyday. But Winnipeg’s grand old buildings have been saved and revived – the downtown Exchange District a model of urban renewal – and it should be your first stop when the business of the day is done.

The Exchange is the historic heart of Winnipeg, today bustling with restaurants, theatres, businesses and artists, many of the old downtown warehouses repurposed as live/work studios and posh loft apartments.

A walking tour with a local guide brings the streets of this National Historic Site to life, from the Pantages Theatre where vaudeville stars such as Buster Keaton and the Marx Brothers trod the boards, to the contemporary architecture of Red River College that cleverly incorporates six heritage buildings within its walls.

Don’t miss the old “newspaper row” where the Winnipeg Free Press News Café offers a taste of local cuisine, with a dash of current events. This experiment by the independent local daily, combining all-day dining with local news, is a first in Canada. Order a plate of Winnipeg smoked goldeye with crème fraiche and crispy potato latkes, and settle in for a political debate or a reading from a local author.

If that sounds too cerebral, you can wander down to Peasant Cookery, where the locally-inspired menu is paired with cool cocktails. Bartender Kaitlynd Landry is inspired by the Manitoba-made Crown Royal rye whisky and will make you a refreshing Blue Divine (fresh blueberries muddled with CR) or the full-on prairie flavours of a Manitoban (CR with beet juice and rhubarb bitters).

Winnipeg is a multi-cultural city with strong French Canadian and aboriginal roots. Just across the Esplanade Riel Pedestrian Bridge, spanning the mighty Red River, you’re in St. Boniface. It’s home to one of the largest French Canadian communities in the West and birthplace of Louis Riel, founder of Manitoba. Visit the French bakeries and cafés along Boulevard Provencher and the museum dedicated to Riel in the old Grey Nuns’ convent, the oldest building in the city.

The Forks, the historic aboriginal meeting place where the Assiniboine River meets the Red, is still a popular place to congregate, whether you’re looking for a bite to eat or a little retail therapy. The old Forks Market is filled with food and craft sellers, and you’ll find chef Michael Schafer’s fine Canadian cuisine at Sydney’s upstairs.

Winnipeg claims one of the highest restaurants-per-capita ratios in North America. You’ll find local ingredients such as bison, pickerel, smoked Winnipeg goldeye and wild rice on many menus, and you’ll also see the city’s Ukrainian, Icelandic, Jewish, French and First Nations heritage reflected in both traditional and contemporary dishes.

Talia Syrie’s idea for helping rejuvenate the dodgier end of downtown is The Tallest Poppy, a hip little diner that’s worth a trip for her big breakfasts and blue-plate-special lunches, featuring organic and local ingredients.

“Where the north end meets the deep south,” she says of the menu that ranges from challah French toast and Chicken-fried Steak & Eggs to pulled pork.

Trendy Osborne Village is another walkable neighbourhood, a popular place to explore for its boutiques and bistros. At Segovia Tapas Bar & Restaurant, chef Adam Donnelly creates innovative, sharable plates with local ingredients, from elk tartare to hangar steak with beet root and horseradish salsa verde, or Berkshire pork belly with sea asparagus. Mr. Donnelly is also a champion of sustainable seafood, and his potted trout with horseradish aioli and seared diver scallops with mint, peas and bacon, are as ethical as they are fun to share.

Another guy to seek out is Alex Svenne, the chef who supervises the volunteers who cook thousands of meals for musicians and staff at the legendary Winnipeg Folk Festival. The rest of the year you’ll find him behind the stoves at his own restaurant, Bistro 7 1/4, also in Osborne Village. Share a bowl of his famous Moules et Frites (he does them 10 different ways) or sink your teeth one of his creative burgers (there’s even one topped with seared foie gras).

At Fusion Grill in nearby River Heights, chef Lorna Murdoch uses Manitoba’s local bounty in creative new ways, from white truffle perogies to pickerel fillets steamed en papillote with lemony Riesling butter and wild rice, all paired with fine Canadian wines.

If you’re looking for an evening’s entertainment, Winnipeg has lots of options. Canada’s Royal Winnipeg Ballet is iconic, and check out the concerts at the historic Pantages Playhouse Theatre.

“Winter-peg” may be a well-deserved nickname, but these resilient Prairie people embrace it. If you’re there in February, stay an extra day for their crazy Mardi Gras parties, or celebrate Festival du Voyageur with the local Francophone community, western Canada’s largest winter festival.

Travelling on business, you might not have your kids in tow, but you can tweet them shots of The Plaza, the massive skateboard park, or find a gift at The Children’s Museum. Otherwise, work out your stresses with an after-work visit to the spectacular hamam spa in the historic Fort Garry Hotel – and think about staying through a weekend the next time you’re in Winnipeg on business.

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